Winter Haven Condos For Sale - 48 condos

Remarks: Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: This move-in-ready home features fresh interior paint, updated countertops, brand-new cabinets, and renovated bathrooms, offering a clean, modern feel throughout. The open-concept floor plan creates a bright and inviting living space, perfect for entertaining or relaxing. Upstairs, a versatile loft provides the ideal spot for a home office, guest area, or flex space to fit your lifestyle. Enjoy low-maintenance living with fantastic community amenities, including a sparkling pool and lake access — perfect for soaking up the Florida sunshine. Ideal for first-time homebuyers, investors or anyone looking for comfort, convenience, and location all in one, this condo offers the perfect blend of style and lifestyle in the heart of Winter Haven. Some photos have been virtually staged to illustrate the property’s potential. Furnishings, décor, and enhancements shown in staged images are for marketing purposes only.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Marquita Smith (863-289-3343)

Remarks: Welcome to your one bedroom one bath 55+ condo located on the FIRST floor. The kitchen features an abundance of cabinetry. Primary bedroom offers 2 built in closets. Front porch area is entirely screened. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Possible Owner Financing Available. Please Inquire with listing agent. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Rosa Suarez (954-682-2633)

Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner.

Listing is courtesy of: LIONHEART BROKERS (321-214-4640)

Listing Agent: Claudia Centesimo (407-383-8882)

Remarks: Welcome to 333 Lake Howard Dr NW, Unit 313A — a beautifully updated 2-bedroom, 2-bath condo located on the top (3rd) floor of a well-maintained 55+ community. The building offers elevator access and is wheelchair accessible, providing both comfort and convenience. This move-in ready unit features large windows in the living room overlooking the community pool, filling the space with natural light and offering peaceful views. Recent updates include all new kitchen cabinets and countertops, a new lanai cabinet, upgraded bathrooms, a new walk-in shower, new carpet throughout, fresh interior paint, new light fixtures, and new vent covers. The roof has also been replaced, adding additional value and peace of mind. Residents enjoy a variety of amenities including a community pool, fitness center, and direct lake access to Lake Howard. The private dock and boat parking make it easy to enjoy fishing, relaxing by the water, or docking your boat — all included in the HOA dues. Additional features include assigned covered carport parking and a 4x4x4 extra storage space located on the 2nd floor. Enjoy low-maintenance living with resort-style amenities in a prime location.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Brian Cox (863-559-3627)

Remarks: PRICE REDUCED on this wonderful opportunity! Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a refrigerator, range, microwave, and dishwasher, plus a walk-in pantry/utility room with in-unit laundry hookups. Relax and unwind on the oversized screened lanai while taking in peaceful views of Lake Conine, perfect for morning coffee or evening unwinding. The home also includes two assigned parking spaces directly in front of the unit, with additional guest parking conveniently located near the clubhouse. Community amenities include a heated swimming pool, clubhouse, shuffleboard courts, and a fishing and boat dock—perfect for enjoying the waterfront lifestyle. The HOA takes care of exterior maintenance, roof upkeep, lawn care, common area landscaping, road maintenance, and pool and dock care, offering truly low-maintenance living. Outdoor enthusiasts will appreciate the public boat ramp across the street providing access to Lake Conine, and the nearby Lake Conine Nature Park (just 0.5 miles away), featuring walking trails, picnic areas, and scenic lake views. Centrally located near shopping, dining, and medical facilities, this property is also just minutes from Legoland and Highway 27, with easy access to Tampa and Orlando. Enjoy comfort, convenience, and lakeside living in one of Winter Haven’s most sought-after condo communities—Winter Ridge.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Michelle Heath (863-528-3123)

Remarks: Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Brian Cox (863-559-3627)

Remarks: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical facilities, Winter Haven Hospital, US Hwy 27, and I-4. The monthly HOA fee covers water, sewer, trash, natural gas, lawn maintenance, grounds upkeep, and use of the community room, allowing for easy, maintenance-free living. An assigned parking space is included, and one pet is welcome with HOA approval (size and breed restrictions apply). Buyer approval is also required by the HOA. Whether you’re searching for a year-round home or a seasonal retreat, this well-maintained condo at Orchid Springs Village offers comfort, convenience, and a welcoming community atmosphere.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Scott Cohara (407-398-9554)

Remarks: Under contract-accepting backup offers. Price Improvement Chain of Lakes Frontage on Lake Hartridge Enjoy true waterfront living in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, part of the renowned Winter Haven Chain of Lakes. Situated in the desirable Casa Del Sol community, this spacious two-story home offers direct lake access and stunning panoramic views. The interior features wood laminate and tile flooring, a formal dining room, updated kitchen with stainless steel appliances and solid surface countertops, and a large living room overlooking the water. Relax in the Florida room or enjoy sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite includes a walk-in closet, ensuite bath with granite counters, and a private enclosed balcony with breathtaking lake views. Two additional bedrooms, full bath, and upstairs laundry complete the layout. An attached 2-car garage adds convenience. Community amenities include a lakefront recreation area, pool, clubhouse, tennis courts, and private dock. HOA covers water, lawn care, and full access to amenities.Experience maintenance-free living with true Chain of Lakes frontage and endless boating, fishing, and waterfront enjoyment.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Irene Bryan (863-289-6789)

Remarks: This spacious 2-bedroom condo features 2 full baths and sits nestled in the back upper corner of the Barcelona building of Orchid Springs! It is NOT a 55+ community, so families and young folks are welcome! This gorgeous condo could be your very own Florida home or investment property. Enjoy stunning views from three sides, with plenty of natural light and air flow only available on end units. Recent upgrades including non-popcorn ceilings, an acoustic ceiling in the kitchen, neutral vinyl plank flooring throughout, and neutral monochromatic ZERO VOC paint. No mismatched floorings or walls, no plastic kitchen ceilings, no carpeting, no outdated popcorn ceilings, and no bedrooms carved out of living room space commonly found in condos. There is an updated full-sized kitchen, not just a galley, that boasts 17 cabinets, 10 drawers & a pantry. It has a spacious great room/dining area, and large primary bedroom easily can handle a king size bed with a full en suite bath & a spacious walk-in closet with hardwood shelves and rods, ready for customization for your personal wardrobe needs! The second bedroom is ample and ready to use for your family member, roommate, or a home office . The stairway is just outside the door, with assigned parking below. And importantly, there is almost zero foot traffic from delivery people or other residents passing in front of this unit since it is the only one on the back side of the stairs in its own little corner! This additional privacy is rare and priceless! You will enjoy walking the ample, lush grounds of Orchid Springs while not having to do outdoor chores in the Florida heat. One small monthly HOA/Management fee (unchanged from 2025) of $312.69 is one of the lowest in this area, and makes this an affordable housing opportunity. The fee covers the building exterior, grounds maintenance, parking lot, laundry & mailroom, common gas water heaters, tree care, water, sewer, trash disposal, gas for heating/cooking if desired, exterior pest control, capital accounts, etc. Of special note is that the electricity SMART meter bank is located in a different building on the first floor, not in this unit, so there is lesser than normal radiation found on a tri-field meter. Also, 5 HOA commercial hot water heaters are in a lower floor common room to serve all of Barcelona, so one less appliance for the homeowner to buy and maintain! Same with the common area HOA laundry facility- no personal washers or dryers to buy or maintain. This unit is around the corner from Legoland, conveniently situated between Orlando & Tampa. Southeast Winter Haven is surrounded by its famous Chain-O-Lakes known for boating, fishing and waterski shows available for you to enjoy! IMPORTANT NOTE: the Barcelona Building and this condominium unit are NOT subject to the statutory engineering inspections and repairs that many high rise condos 3+ stories tall are, thus eliminating the potential associated astronomical, unanticipated assessments that may occur as a result.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Karel Cain (863-287-0196)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of Polk County. This is a second-floor unit with 2 bedrooms, 2 bathrooms, and is ready to move into. This is a 55+ community and has a nice square footage for this lifestyle. Many amenities are included in the HOA fee structure - lawn, water, sewer, natural gas, grounds, clubroom. The dishwasher is in as-is condition. This is a secluded area with no noise behind you (maybe a squirrel), but more peace and tranquility. Text, call, email, and see it today! Agents, please see MLS (Realtor) remarks.

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Buyer defaulted, check out this great value. The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of East Polk County. This is a 2nd-floor unit in Orchid Springs that is ready to move into NOW! The home has fresh paint throughout and brand new carpet. This is a one-bedroom, open floor plan with most of all utilities bundled in the HOA fees - to include - community pool, gas, exterior maintenance, maintenance grounds, water, sewer, trash. It has an approximate of 1,078 square feet of living, a dedicated parking space, and a common laundry area. Great with overlooking the preserve of nature's own form and the extremely quiet area of the Orchid Springs compound. Text, call, or email for viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings. Inside, you'll love the bright, open layout with 10' ceilings, rich wood cabinetry, and a breakfast-bar kitchen—ideal for casual meals, morning coffee, or entertaining. Both bedrooms feature spacious walk-in closets, plus you'll appreciate the extra outdoor storage for bikes, golf gear, and more. Enjoy the benefits of a low HOA that covers exterior maintenance, landscaping, pest control, and trash, along with access to the community pool and tennis courts. Cypresswood residents also enjoy resort-style amenities, including an 18-hole Ron Garl-designed golf course, clubhouse, restaurant, and junior Olympic pool. Ideal for first-time buyers, families, professionals, golf enthusiasts, seasonal residents, or investors seeking a turnkey rental in a premier gated community. Prime location: Minutes to I-4 and Hwy 27 for easy commuting. Close to LEGOLAND, Bok Tower Gardens, shopping, dining, medical facilities, and entertainment. Centrally located between Tampa and Orlando—the best of Central Florida at your doorstep. Don't miss this opportunity! Pond-view units in Cypresswood are highly desirable and move quickly. Schedule your private showing today and see why Cypresswood is such a wonderful place to call home.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: One or more photo(s) has been virtually staged. Downtown Winter Haven condo located in one of Winter Haven’s most iconic hotels, The Haven. This residence has been transformed into boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. With its blend of vintage charm, modern updates, and low-maintenance living, this 1-bedroom, 1-bath unit is ideal for first-time buyers, investors, seasonal residents, or anyone seeking an affordable condo with great rental potential. Located on the 3rd floor, the residence features tall ceilings, large windows, and bright natural light with elevated views of downtown. The updated kitchen offers granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets—perfect for maximizing storage in a condo setting. The spacious primary bedroom boasts oversized historic windows, a walk-in closet, and room for a king-sized bed. The bathroom has been refreshed with granite counters, a tiled tub surround, and a traditional tub/shower combo. The Haven provides sought-after condo amenities, including secure key-fob access, elevators, a community pool, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby. Residents also enjoy a private pool courtyard surrounded by lush landscaping, creeping fig walls, palm trees, and peaceful lounging areas—ideal for relaxation or working remotely outdoors. This walkable location offers the best of downtown Winter Haven living. Enjoy immediate access to dining, shopping, entertainment, and lakefront walking paths. With 50 lakes—including the world-famous Winter Haven Chain of Lakes—you’re minutes from boating, fishing, skiing, and sunset views. Everyday conveniences like Publix, Walmart, Aldi, TJ Maxx, medical facilities, and LEGOLAND Florida Resort are all close by. If you’re looking for an affordable, updated, low-maintenance condo with historic character and the convenience of downtown living, this stylish unit at The Haven checks every box.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!

Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)

Listing Agent: Vincent Reina (863-398-6243)

Remarks: First Floor condo offers comfortable, low-maintenance living with numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Nancy Cini (727-612-0375)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy peaceful lakefront living in this beautifully updated 2-bedroom, 2-bath condo in the gated Winterset community. With an open floor plan, granite countertops, stainless-steel appliances, upgraded cabinets, and a cozy breakfast nook, this home blends style and comfort. The enclosed balcony offers stunning Garden Lake views, perfect for relaxing mornings or golden evenings. Recent updates include new plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout. Winterset features resort-style amenities—pool, spa, clubhouse, tennis and pickleball courts, plus a private pier for fishing or kayaking. Located just 5 minutes from LEGOLAND and under an hour to Disney, this move-in-ready home delivers Florida living at its best. Sale subject to lender approval. SHORT SALE APPROVED at $170,000 (Appraised Value). Great opportunity for investors, first-time buyers, or a winter retreat.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Valerie Howze (863-604-9080)

Remarks: Cozy 2 bedroom 2 bath home with great view of Lake Howard off the master bedroom and patio. Turn around and look out of the front door with a beautiful view of the pool and patio areas. Rood is new this year with all damage from last year's storm repaired. This home is in move-in condition.

Listing is courtesy of: CHOICE PROPERTIES OF CENT FL (863-299-6710)

Listing Agent: Jane Tyl (863-224-1779)